


Sammy's Ass Started It All

by DieTheSlashAddict



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Barebacking, Condoms, Dead Dove: Do Not Eat, Dean Winchester/Original Male Characters - Freeform, Drugged Sex, Dry Orgasms, Extreme Underage, Felching, First Time, Gang Bang, Hand Jobs, Incest, Just the Tip, M/M, Multi, Non-Consensual Somnophilia, Pedophilia, Rimming, Sex for Money, Underage - Freeform
Language: English
Status: Completed
Published: 2018-12-11
Updated: 2018-12-11
Packaged: 2019-09-16 07:14:43
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 2
Words: 2,494
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16949439
Author URL: https://archiveofourown.org/users/DieTheSlashAddict/pseuds/DieTheSlashAddict
Summary: Dean couldn't keep his eyes off Sammy's luscious ass. Eventually Sammy's spring allergies give him an excuse, and also a plan for how they can make some extra cash while dad is away.





	1. Diphenhydramine

Puberty was a cold bitch. Dean had decided that last year when hair started showing up everywhere and his dick wouldn’t stop getting hard over nothing. Dad had sat him down and had the talk with him after he caught him surfing pay per view porn at a motel. At 12 years old Dean was apparently an early bloomer. And it was not ok.  
The worst part? Was Sam. Sam was in a growth spurt, all long legs and baby fat dripping away. The only part of him that was still bouncy and glorious was his ass. Dean tried everything not to notice that ass. His eight-year-old brother should not be such a subject of fascination. But Dean caught himself time and again watching Sam. He knew he would never touch him though, he was sure he had the will power.  
He had fooled around with a few girls, even gotten to third base and felt the burning hot wetness of her insides. But it was nothing compared to what he felt watching little Sammy parade naked around the hotel room when Dad was gone. He took so many cold showers that spring.  
Suddenly it was spring break, and Dad had paid up for the hotel for two weeks, given Dean 100 dollars for food and left for a hunt. It sounded like heaven to them. They were in Oklahoma, so it was warm enough that the pool was open, and they spent many long days out their splashing around and getting nice and brown. Sammy tanned beautifully, while Dean mostly burned.  
One bad thing they found was the pollen. It was thick and yellow and gross, and Sam was a miserable ball of misery most days. Dean checked the available money. He would need to supplement it some how, and when the idea came to him, he almost threw up. But he knew it was the perfect plan.  
He wandered down town and stopped by a pharmacy, and then headed to a seedy bar. When he got back to the hotel Sam was huddled up and sniffling. Dean pulled out his surprise and handed Sam an adult strength Benadryl. Sam took it gratefully and it wasn’t 30 minutes later that he was asleep. Dean licked his lips and contemplated his plan. He knew the medicine would keep Sam asleep for hours, but he wasn’t sure how deep he would sleep. So, he started off innocently, stripping Sam’s pjs and underoos. Sam didn’t even twitch. Dean rolled him onto his belly to put that perfect ass on display. His cock was already rock hard.  
He pulled out a tube of lube, glad that there wasn’t an age limit on its purchase and poured some on his fingers. He warmed it up and leaned down over Sammy, who was half hanging off the bed now, and ran a finger over that perfect pink hole. It was to much and he sunk his finger in slowly, feeling Sammy’s. Oct respond to the intrusion and try to push him out. But he just pushed in further, teasing him open with his fingers for a good half hour before he decided Sam was open enough. Now for the good part. He dropped his pants and slicked his own cock.  
That moment of pressing in will always be with him. The slick burning goodness of his baby brother opening up for him. He would be ashamed by how quick he was. It was barely a dozen thrusts before he came, filling his little brother with his come. He knew in that moment it wouldn’t be the last time. He pulled out and spent a few more minutes playing with Sam’s hole, stretching it and squirting lube directly in it before he sent off the text.  
Ten minutes later there was a knock at the door. Dean opened it and was greeted by five men, ranging in age from twenties to fifties. He ushered them in quickly and they all stared at Sam in awe.  
“Fucking beautiful man. How much?” The youngest asked, Dean looked him over, designer shoes and a brand-new leather coat.  
“500? Each?” he asked, and the men groaned a bit, but all started digging in their wallets.  
“Some ground rules. Condoms. And you have to be gentle. I want to be able to explain this in the morning and if he’s bleeding I can’t. No marks either. I want you to go in order of cock size smallest first, to make sure he’s opened up. So, hand over the money and drop your pants.” The men looked uncomfortable, but they kept glancing at Sam and finally they complied. And Dean had 2500 dollars in his pocket and five cocks to examine.  
The oldest guy went first, his dick was only about five inches and not very thick. Barely bigger then Dean’s own cock. He put on the condom without a fuss and slowly entered the sleeping boy. Sam still didn’t stir but his breathing picked up. The guy was apparently pent up because it was all of two minutes before the guy came with a groan and pulled out. The next guy was probably six inches and decently thick, and he also stepped forward and put on a condom and pressed inside with a groan.  
“Fuck he’s so tight. I didn’t know anyone could be this tight.” He gasped, fucking in rough enough that Dean had to admonish him. He slowed down, fucking deep and steady and made it a whole five minutes. The next one was middle aged, probably mid 40s, and his cock was long and thin. He also took the longest, a full ten minutes before he came with a shout that surprisingly didn’t wake the neighbors, and definitely didn’t wake Sam.  
Dean checked Sam’s pulse, always worrying and it was strong and steady, as was his breathing. Fourth guy stepped up, the youngest. And he pulled out a cock that had Dean’s jaw dropping. Nine inches at least and thicker then all the rest so far. Dean looked at it, intimidated, and a bit turned on. The man rolled his eyes.  
“I’ll be really gentle, this isn’t my first time with a young boy.” And as disturbing as that statement was, it was also comforting. He put on a condom and positioned himself, sliding in painfully slow with a look of adoration on his face. Dean’s cock twitched and started to fill in his jeans. The man went slow, painfully so, and was gentle as he thrust shallowly into Sammy’s sweet ass. He lasted ten minutes at least, watching Dean with a look of fascination as he fucked Sam. It made his skin crawl and his dick harden. When the man finally came it was with a look of bliss. He pulled out slowly, savoring it. Sammy rolled in his sleep and they all stared at him in silence. Until they were sure he was still out.  
Dean gestured for the last man, a black man in his early thirties, Dean would guess. And the man grinned and stroked his monster of a cock. Dean looked at it and bit his lip, imagining what that thing could do to Sammy. “Be careful, you could do real damage with that.” The man laughed and nodded.  
“I know, I’ll probably only be able to fit about half, but that’s enough.” He also slid a condom on and proceeded to line up for Sam’s abused hole. He pressed in, feeling resistance at first and gasping when the head slid in with a pop. Dean’s cock was leaking at this point and he rubbed the heel of his hand over his hard cock as he watched that big cock spread his brother open.  
While the last man fucked Sammy, the youngest one approached him.  
“How much for you? Those cock sucking lips need put to good use and your ass is almost as good as his. Plus. I like my lovers moving and reacting. Not like that.” He said, gesturing towards Sammy’s body as it rocked with the thrusts of the powerful man. Dean bit his lip. 

“What are you offering?” he asked, knowing he would say yes. The rich young man grinned and pulled out a wad of bills and counted out 6000. “This? On top of what we’ve already paid?” Dean looked at the money and did the math.  
“Make It seventy-five, so we have an even 10?” he said, voice braver then he felt. The man smirked and peeled off a few more bills.  
“Now get naked.” And Dean…well he had been taught to take orders. He heard the last man come and pull out from Sammy and he looked around at the eager onlookers, most stroking their cock back to hardness as they watched. He shrugged and started stripping.


	2. For the money

**Summary for the Chapter:**

> Dean's turn.

Dean didn’t even know the name of the guy with half his hand in his ass. He did know that every once and awhile he would hit a spot that would make Dean scream. The youngest had started since it was his idea. And he was prepping Dean carefully and slowly. Dean was sloppy with lube and the man was determined to get a fourth finger in Dean’s virgin hole.   
Dean realized pretty quickly that he loved it. And when Young and Rich finally slid home Dean howled, his cock spurting all over the bed covers. Young and Rich just grinned and started fucking into him harder. Hitting his prostate on every thrust. Dean was almost ready to come again when Young and Rich moaned and twitched out his own orgasm.   
Next was Big and Black and Dean shivered at seeing the monster cock all over again. But it slid in easy, feeling fantastic stretching him in all the right ways. Dean was moaning and fucking himself back on it immediately and he could hear the other guys laughing but he didn’t care. He was so close. One hard thrust straight to his prostate had him coming for the third time that night and he was definitely exhausted. But there were three more to go.

Old and Small was quick, and he didn’t even try to get Dean off, just rabbited away inside him until he filled him with come. It was only then that Dean realized they weren’t using condoms. But he couldn’t bring himself to care, especially when Unremarkable Six inches got down on his knees and started sucking it out. Dean cried out, hips jerking back and trying to get more. He was sure the guy smirked when he stood up and slid in, his cock felt nice, but like nothing compared to what had come before, and Dean rocked back quicker trying to get more stimulation. The guy laughed and gripped Deans hips tight enough to bruise as he fucked him rough and fast. Dean was gasping, and his cock was leaking again by the time the guy finished. Dean collapsed, panting but still hard, into the mattress.   
One more to go and it’s Fortyish and Thin, and Dean’s not sure his ass can handle anymore. He sympathizes with the sleeping Sammy, who got their worst. But the guy climbs up on the bed and lays top to tail with Dean.   
“Let me try out those pretty lips ok? And I’ll make you come like you never have before.” Dean nodded, nervous because this wasn’t something he had done before but he leaned forward and licked the cock in front of him earning him an encouraging moan. That was enough to get him to take him into his mouth and suck, feeling like a natural as he swirled his tongue and teased the head. When the man swallowed him down, he moaned around the cock in his mouth and that made the man moan again.   
Fortyish and Thin reached between Dean’s legs and sunk two fingers in his sloppy hole and nailed his prostate while still sucking and Dean choked, pulling off to catch his breath as he moaned and rocked his hips back and forth into both stimulations. He went back to work though, sucking harder and bringing a hand up to gently caress the springy hair on the man’s balls. The man groaned at that and it was enough to have Dean coming, moaning around the cock in his mouth and suddenly choking on a bitter load of come. He swallowed it down and pulled off with a groan.   
“Fuck. Ok…get dressed and get out, ok?” And not a man hesitated to do so. They left a six pack and another couple hundred on the table as they filed out, looking pleased and relaxed.   
Dean was sweaty and exhausted and most annoyingly covered in come, his own and other’s so he went and had a shower. When he came out, he found Sammy awake and crying. He immediately dropped to his knees next to him.

“What’s wrong Sammy? Did you have a bad dream?” Sammy shrugged and pulled the blankets around him.   
“I don’t know. I just…I hurt…down there. “he whispered. And Dean felt his cock fill again.   
“You mean your butt?” he asked, and Sam nodded and shook his head.   
“And my boy parts are all…hard and achy.” He said, and Dean’s life flashed before his eyes.   
“Yeah that can happen. I have an idea that will make it better though. It sounds a bit weird, but it will feel good I promise.” Sammy frowned but nodded, always trusting in Dean’s guidance. Dean suppressed a grin and instead gave a comforting smile. “Turn over and show me your butt ok baby boy?” And Sam blushed but did it, getting up on his hands and knees to present himself.  
Dean drooled. But he leaned in and ran his tongue gently across the bruised hole. Sammy made a strange noise but rocked back into it and Dean went to town, just like Unremarkable and Six inches had done to him. Sam started whimpering in what sounded like discomfort and Dean saw him trying to rub his cock against the mattress. Dean reached between his legs and grabbed his little cock and started stroking it.   
Sam cried out and his whole body went rigid, his hole clenching around Dean’s tongue and he cried out, his cock twitching but nothing came out as he writhed. He collapsed into the mattress and Dean let him go. He patted Sammy’s luscious ass, the reason they had gotten into this whole mess and realized Sammy was asleep again. He looked at Sam’s hole and down to his own hard cock and couldn’t resist a little.   
He stroked himself off, staring at Sammy’s ass, and right when he was about to come, he popped the head in and shot his load into his sleeping brother.   
Dean went to sleep that night feeling like a new man and about 11000 dollars richer. Fucking hell. He thought he might love puberty.


End file.
